JP2987682B2 - 酸性リン脂質の濃縮法 - Google Patents
酸性リン脂質の濃縮法Info
- Publication number
- JP2987682B2 JP2987682B2 JP7151260A JP15126095A JP2987682B2 JP 2987682 B2 JP2987682 B2 JP 2987682B2 JP 7151260 A JP7151260 A JP 7151260A JP 15126095 A JP15126095 A JP 15126095A JP 2987682 B2 JP2987682 B2 JP 2987682B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- lecithin
- lower alcohol
- phospholipid
- phospholipids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003904 phospholipids Chemical class 0.000 title claims description 86
- 230000002378 acidificating effect Effects 0.000 title claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 87
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 37
- 239000000787 lecithin Substances 0.000 claims description 35
- 235000010445 lecithin Nutrition 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 34
- 229940067606 lecithin Drugs 0.000 claims description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 13
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 12
- 229940083466 soybean lecithin Drugs 0.000 claims description 12
- 150000003905 phosphatidylinositols Chemical class 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 240000002791 Brassica napus Species 0.000 claims description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 description 17
- 230000007935 neutral effect Effects 0.000 description 13
- 239000012046 mixed solvent Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 9
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 8
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 5
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 4
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000019640 taste Nutrition 0.000 description 4
- WRGQSWVCFNIUNZ-GDCKJWNLSA-N 1-oleoyl-sn-glycerol 3-phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O WRGQSWVCFNIUNZ-GDCKJWNLSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 229930186217 Glycolipid Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000008347 soybean phospholipid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 triglyceride Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 102000011420 Phospholipase D Human genes 0.000 description 1
- 108090000553 Phospholipase D Proteins 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Cosmetics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7151260A JP2987682B2 (ja) | 1995-06-19 | 1995-06-19 | 酸性リン脂質の濃縮法 |
| US08/656,050 US5833858A (en) | 1995-06-19 | 1996-05-31 | Method of concentration of acidic phospholipid |
| EP96109319A EP0749693B1 (en) | 1995-06-19 | 1996-06-11 | Method of concentration of acidic phospholipid |
| DE69623191T DE69623191T2 (de) | 1995-06-19 | 1996-06-11 | Verfahren zur Konzentration von saurem Phospholipid |
| CN96110929A CN1066738C (zh) | 1995-06-19 | 1996-06-19 | 酸性磷脂的浓缩方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7151260A JP2987682B2 (ja) | 1995-06-19 | 1995-06-19 | 酸性リン脂質の濃縮法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09165A JPH09165A (ja) | 1997-01-07 |
| JP2987682B2 true JP2987682B2 (ja) | 1999-12-06 |
Family
ID=15514780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7151260A Expired - Fee Related JP2987682B2 (ja) | 1995-06-19 | 1995-06-19 | 酸性リン脂質の濃縮法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5833858A (zh) |
| EP (1) | EP0749693B1 (zh) |
| JP (1) | JP2987682B2 (zh) |
| CN (1) | CN1066738C (zh) |
| DE (1) | DE69623191T2 (zh) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9823837D0 (en) * | 1998-10-30 | 1998-12-23 | St Ivel Ltd | Edible emulsion |
| GB9823836D0 (en) * | 1998-10-30 | 1998-12-23 | St Ivel Ltd | Edible emulsion |
| US6833149B2 (en) * | 1999-01-14 | 2004-12-21 | Cargill, Incorporated | Method and apparatus for processing vegetable oil miscella, method for conditioning a polymeric microfiltration membrane, membrane, and lecithin product |
| IT1319679B1 (it) | 2000-12-05 | 2003-10-23 | Chemi Spa | Processo di purificazione di fosfatidilserina. |
| HUP0401020A3 (en) * | 2000-12-21 | 2005-09-28 | Unilever Nv | Food composition suitable for shallow frying comprising sunflower lecithin |
| IL147529A0 (en) * | 2002-01-09 | 2002-08-14 | Oladur Ltd | A method for the production of soybean sugars and the product produced thereof |
| AU2003261218A1 (en) * | 2002-07-23 | 2004-02-25 | Solae, Llc | Process for removing sugar and/or oil from lecithin |
| NZ523920A (en) | 2003-01-31 | 2005-11-25 | Fonterra Co Operative Group | Methods for extracting lipids from diary products using a near critical phase fluid |
| WO2004107875A1 (ja) * | 2003-06-06 | 2004-12-16 | Nagase Chemtex Corporation | リン脂質含有乳化性組成物 |
| US7825270B2 (en) * | 2005-12-21 | 2010-11-02 | Nutrimed Biotech | Inositolphospholipids and analogues: phosphatidylinositol products and processes |
| US8877239B2 (en) * | 2010-08-12 | 2014-11-04 | Nutritional Therapeutics, Inc. | Lipid supplements for maintaining health and treatment of acute and chronic disorders |
| US11247964B2 (en) | 2009-05-01 | 2022-02-15 | Rrip, Llc | Method of processing phospholipid based lipid materials |
| MY161428A (en) | 2012-09-12 | 2017-04-14 | Sime Darby Malaysia Berhad | Extracting Lecithin From Palm Agro-Waste |
| JP6295263B2 (ja) | 2012-10-24 | 2018-03-14 | カーギル インコーポレイテッド | リン脂質の含有材料からの画分化方法 |
| JP6280557B2 (ja) * | 2012-10-24 | 2018-02-14 | カーギル インコーポレイテッド | リン脂質含有乳化剤組成物 |
| JP6542408B1 (ja) * | 2018-02-21 | 2019-07-10 | 丸大食品株式会社 | リン脂質濃縮物生産方法 |
| CN113717220A (zh) * | 2021-10-11 | 2021-11-30 | 江苏曼氏生物科技股份有限公司 | 一种大豆磷脂中糖脂去除工艺 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE253758C (zh) * | ||||
| GR74979B (zh) * | 1980-10-02 | 1984-07-12 | Unilever Nv | |
| JPH07108194B2 (ja) * | 1986-10-23 | 1995-11-22 | 昭和産業株式会社 | 燐脂質を含有する食品の製造法 |
| JPH01277457A (ja) * | 1988-04-27 | 1989-11-07 | Kao Corp | レシチンの精製方法 |
| US5214171A (en) * | 1988-12-08 | 1993-05-25 | N.V. Vandemoortele International | Process for fractionating phosphatide mixtures |
| JPH0732674B2 (ja) * | 1989-06-12 | 1995-04-12 | 日清製油株式会社 | 油脂組成物 |
| EP0495510A3 (en) * | 1991-01-18 | 1993-03-31 | Kao Corporation | Phospholipid composition, fat and oil composition containing the same and process for producing phosphatidic acids |
| JPH0597872A (ja) * | 1991-10-03 | 1993-04-20 | Shokuhin Sangyo High Separeeshiyon Syst Gijutsu Kenkyu Kumiai | ホスフアチジルイノシトールの分離・精製法 |
| JP3032357B2 (ja) * | 1991-11-08 | 2000-04-17 | 雪印乳業株式会社 | リン脂質画分の分画精製方法 |
| US5319116A (en) * | 1992-02-12 | 1994-06-07 | Gary Viole | Lecithin fractions and dilutions, methods for their preparation and pharmacological uses thereof |
| US5407921A (en) * | 1993-07-01 | 1995-04-18 | Kao Corporation | Method for suppressing bitter taste |
-
1995
- 1995-06-19 JP JP7151260A patent/JP2987682B2/ja not_active Expired - Fee Related
-
1996
- 1996-05-31 US US08/656,050 patent/US5833858A/en not_active Expired - Lifetime
- 1996-06-11 DE DE69623191T patent/DE69623191T2/de not_active Expired - Lifetime
- 1996-06-11 EP EP96109319A patent/EP0749693B1/en not_active Expired - Lifetime
- 1996-06-19 CN CN96110929A patent/CN1066738C/zh not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 特開 平３−５８９９４ＪＰ，Ａ） |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1066738C (zh) | 2001-06-06 |
| CN1145368A (zh) | 1997-03-19 |
| JPH09165A (ja) | 1997-01-07 |
| DE69623191D1 (de) | 2002-10-02 |
| US5833858A (en) | 1998-11-10 |
| DE69623191T2 (de) | 2003-04-10 |
| EP0749693A2 (en) | 1996-12-27 |
| EP0749693A3 (en) | 1998-09-16 |
| EP0749693B1 (en) | 2002-08-28 |
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